JPS5942643B2 - Nematicide - Google Patents

Description

【発明の詳細な説明】 本発明は１，５，５．５−テトラクロルペンテン−２を
有効成分とする殺線虫剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a nematicide containing 1,5,5,5-tetrachloropentene-2 as an active ingredient.

従来より、土壌中に棲息して植物の根部に寄生し、その
正常な発育を阻害する種々の植物寄生性線虫類の駆除の
ため、■、２−ジブロムエタンＢｒ −ＣＨ２ＣＨ２Ｂ
ｒ（ＥＤＢ）、■、２−ジブロムー３−クロルプロパン
ＢｒＣＨ２ＣＨＢｒＣＩ−（２Ｃ４（ＤＢＣＰ ）や１
゜３−ジクロルプロペン及び１，２−ジクロルプロパン
等の混合物Ｃ＃ＣＨ＝ ＣＨＣＨ２Ｃ７＋ＣＨ３ＣＨＣ
ｄＣＨ２Ｃ７（Ｄ−Ｄ）などのハロゲン化炭化水素類を
用いることは良く知られている。Conventionally, 2-dibromoethane Br -CH2CH2B has been used to exterminate various plant-parasitic nematodes that live in the soil, parasitize the roots of plants, and inhibit their normal development.
r(EDB), ■, 2-dibromo-3-chloropropaneBrCH2CHBrCI-(2C4(DBCP) and 1
゜Mixture of 3-dichloropropene, 1,2-dichloropropane, etc. C#CH= CHCH2C7+CH3CHC
The use of halogenated hydrocarbons such as dCH2C7 (D-D) is well known.

しかし、ＥＤＢやＤ−Ｄは土壌中に施用する際に特殊な
注入器を用いて土中に注入し、更にＤ−Ｄなどでは蒸気
圧が高いため施用後ビニールシートなどの被覆材で土壌
の表面を被覆して薬剤の揮散を防止する必要があり、ま
た、栽培作物に対する強い薬害のため処理後は充分なガ
ス抜を行い、しばらくは播種、植付ができない等の難点
を有し、更にはＤＢＣＰなどのように人体に対する毒性
上（発ガン性）の問題からその製造、使用（こついて行
政上の制限を受けているものもあり、実用上程々の欠点
を有している。However, when applying EDB and D-D into the soil, they are injected into the soil using a special injector, and because D-D and other products have high vapor pressure, they are covered with a covering material such as a vinyl sheet after application. It is necessary to cover the surface to prevent the volatilization of the chemical, and since the chemical is highly harmful to cultivated crops, sufficient degassing must be performed after treatment, making it impossible to sow or plant for a while. Some of them, such as DBCP, are subject to administrative restrictions on their manufacture and use due to their toxicity (carcinogenicity) to the human body, and they have considerable drawbacks in practical use.

本発明の１．５，５．５−テトラクロルペンテン−２は
次の構造式Ｃ１ＣＨ２ＣＨ−ＣＨＣＨ２ＣＣ１３で表わ
されるハロゲン化炭化水素の一種であるが、前記既存の
殺線虫剤に較べ優れた殺線虫効果を有し、比較的少量で
も有効であり、しかも、その施用ζこ際しては必ずしも
注入処理によるはかりでなく土壌混和処理或いは播溝処
理等の方法でも充分な効果を発揮し、また作物に対する
薬害や人畜に対する毒性も低く、取扱い上剥激臭や催涙
性も殆んどない等優れた利点を有する。The 1,5,5,5-tetrachloropentene-2 of the present invention is a type of halogenated hydrocarbon represented by the following structural formula C1CH2CH-CHCH2CC13, and it has an excellent nematicidal effect compared to the existing nematicides. It has an insect effect and is effective even in a relatively small amount, and its application is not necessarily by injection, but also by methods such as soil mixing or trenching, and It has excellent advantages such as low chemical damage to crops and low toxicity to humans and livestock, and almost no strong odor or lachrymation when handled.

本発明の化合物は上記の如く、両端の炭素原子（こｌ又
は３の塩素原子が結合し且中間に炭素−炭素２重結合が
存在するという特徴的構造を有゛する化合物であるが、
因みＯこ、同じ炭素数の塩素化炭化水素でも炭素−炭素
２重結合が飽和している化合物である１、１，１．５−
テトラクロルペンタンＣｌＣＨ２ＣＨ２ＣＨ２ＣＨ２Ｃ
Ｃｌ３や２重結合が炭素鎖の末端にある化合物である１
＋ １．５−ト’）クロルペンテン−ＩＣ１２Ｃ−Ｃ
ＨＣＨ２ＣＨ２ＣＨ２Ｃ４では殺線虫効果は半分以下に
低下し、また塩素原子が末端の炭素原子ではなく中間の
炭素原子に結合している化合物である１、１，１，３−
テトラクロルペンタン められなかった。As mentioned above, the compound of the present invention is a compound having a characteristic structure in which carbon atoms (one or three chlorine atoms) are bonded at both ends and a carbon-carbon double bond is present in the middle.
Incidentally, chlorinated hydrocarbons with the same number of carbon atoms are compounds with saturated carbon-carbon double bonds, 1, 1, 1.5-
Tetrachlorpentane ClCH2CH2CH2CH2C
Cl3 or a compound in which the double bond is at the end of the carbon chain1
+ 1.5-t') chlorpentene-IC12C-C
In HCH2CH2CH2C4, the nematicidal effect is reduced by more than half, and in addition, 1,1,1,3-, which is a compound in which the chlorine atom is bonded to the middle carbon atom rather than the terminal carbon atom.
I couldn't taste tetrachlorpentane.

尚、本発明化合物は従来公知の種々の有機合成手段を用
いて製造することができるが、一例を示せば、ジャーナ
ル、オブ、ケミカル、ソサエティ、１９６３年第１８８
７頁ζこ記載の方法に準じて、適当な溶媒中で金属塩化
物を共存させてブタジェンと四塩化炭素を加熱下に反応
させる方法等σこより容易に且経済的ζこ実施すること
ができる。The compound of the present invention can be produced using various conventionally known organic synthesis methods, but one example is as described in Journal of Chemical Society, No. 188, 1963.
Page 7 ζ According to the method described here, a method in which butadiene and carbon tetrachloride are reacted under heating in the coexistence of a metal chloride in a suitable solvent, etc. can be carried out more easily and economically. .

次ζこ代表的な合成例を示して更に具体的に説明する。Next, a typical synthesis example will be shown and explained in more detail.

合成例 耐圧ガラスビンにブタジェン２７！！、四塩化炭素１６
０ｇ、塩化第２銅０．４ｇ、ジエチルアミン塩酸塩２ｇ
、アセト二ｌ−ＩＪル６０ｍ１を仕込み、１００°Ｃｔ
こ加熱して６時間反応させた。Synthesis example Butadiene 27 in a pressure-resistant glass bottle! ! , carbon tetrachloride 16
0g, cupric chloride 0.4g, diethylamine hydrochloride 2g
, charged 60ml of acetonyl-IJ and heated to 100°Ct.
The mixture was heated and reacted for 6 hours.

反応後反応生成物を水洗した後減圧下に蒸留して１，５
゜５．５−テトラクロルペンテン−２（沸点１０８〜１
１２°Ｃ／ ２５ ｍｍ珪わ９２，９を得た。After the reaction, the reaction product was washed with water and distilled under reduced pressure to give 1,5
゜5.5-Tetrachloropentene-2 (boiling point 108~1
A 12°C/25 mm slit 92.9 was obtained.

収率８８．５％。但し、上記は単なる例示であって本発
明化合物の合成法としては何ら制限されないことは言う
迄もない。Yield 88.5%. However, it goes without saying that the above is merely an example and is not intended to limit the method of synthesizing the compound of the present invention.

本発明の殺線虫剤は土壌中に棲息し、植物の根や塊茎等
の地下部に寄生する各種線虫類、例えばサツマイモネコ
ブセンチュウ、キタネコブセンチュウ、アレナリアネコ
ブセンチュウ、リンゴネコブセンチュウ等のネコブセン
チュウ、ダイズシストセンチュウ、ムギシストセンチュ
ウ、オカボシストセンチュウ、バレイショシストセンチ
ュウ、ビートシストセンチュウ等のシストセンチュウ、
ミナミネグサレセンチュウ、キタネグサレセンチュウ、
ムギネグサレセンチュウ、クルミネグサレセンチュウ、
チャネグサレセンチュウ等のネグサレセンチュウその他
ワセンチュウ、サヤワセンチュウ、ビンセンチュウ、ラ
センセンチュウ、ミカンネセンチュウ、イシュクセンチ
ュウ、ユミハリセンチュウ等の外部寄生線虫や土壌中よ
り植物体に侵入し葉、花、茎等の地上部０こ寄生して被
害を及ぼすイチゴセンチュウ、ハガレセンチュウ等のハ
センチュウやクキセンチュウ等広範な線虫の駆除に用い
られる。The nematicide of the present invention is applied to various nematodes that live in the soil and parasitize underground parts such as roots and tubers of plants, such as nematodes such as sweet potato nematode, northern nematode, arenaria nematode, apple nematode, and soybean cyst. Cyst nematodes such as nematode, wheat cyst nematode, okabo cyst nematode, potato cyst nematode, beet cyst nematode,
Minami Negusare nematode, Northern Negusare nematode,
Muginegusare nematode, Walnut negusare nematode,
Ectoparasitic nematodes such as Negusare nematode such as Chanegusare nematode, other nematode nematodes such as Vanilla nematode, Sayawa nematode, Vin nematode, Rasen nematode, Citrus nematode, Ishuku nematode, Yumi nematode, etc., and invade the plant body from the soil and invade the leaves and flowers. It is used to exterminate a wide range of nematodes such as strawberry nematodes, leaf nematodes, and other nematodes that parasitize above-ground parts of stems and cause damage.

本発明化合物はそのままでも用いられるが、必要σこ応
じて油剤、乳剤、水利剤、粒剤、微粒剤、粉剤等の農薬
製剤上慣用されている各種製剤として施用することがで
きる。The compounds of the present invention can be used as they are, but depending on the needs, they can be applied in the form of various formulations commonly used in agrochemical formulations, such as oil solutions, emulsions, irrigation solutions, granules, fine granules, and powders.

その際、製剤形態に適合した液体又は固体状の各種溶剤
担体、希稀剤、増量剤、界面活性剤等の当該技術に於い
て常用の補助剤が用いられる。At this time, adjuvants commonly used in the art such as various liquid or solid solvent carriers, diluents, fillers, surfactants, etc., which are compatible with the formulation form, are used.

また、更に他の農薬活性成分と混用又は併用することも
できる。Moreover, it can also be mixed or used in combination with other agricultural chemical active ingredients.

本発明の殺線虫剤は施用に当り、液剤を土壌中に注入す
る方法以外にも潅注覆土処理や粒剤、粉剤等を播溝に散
布して土寄せする方法或いは土壌混和処理等いずれの方
法でも良く、また、作物の作付前処理のみならず、場合
によっては生育中の立毛処理も可能である。When applying the nematocide of the present invention, in addition to the method of injecting the liquid agent into the soil, any method such as irrigation and soil-covering treatment, spraying granules, powders, etc. into the seeding furrow to cover the soil, or soil mixing treatment can be used. Moreover, not only pre-planting treatment of crops but also hair-standing treatment during crop growth may be possible.

施用量としては通常、有効成分量として１〜３０ｋｇ／
１０ａ１好ましくは５〜２０ｋｇ／１０ａ８度が適当で
ある。The amount of application is usually 1 to 30 kg/as the amount of active ingredient.
10a1 is preferably 5 to 20 kg/10a8 degrees.

しかし、これは一応の目安であり具体的には例えば、対
象となる作物の種類、線虫の種類、被害の程度、剤形、
施用法、土壌条件、季節、天候等により適宜加減して用
いられる。However, this is only a rough guideline, and specific examples include the type of target crop, type of nematode, degree of damage, dosage form,
The amount may be adjusted as appropriate depending on the application method, soil conditions, season, weather, etc.

一般的に言えば本発明の殺線虫剤は従来市販のＤ−Ｄや
ＤＣＩ Ｐ （ジクロルジインプロピルエーテル）など
と較べて比較的少量でも充分な効果が得られる。Generally speaking, the nematicide of the present invention can be sufficiently effective even in a relatively small amount compared to conventional commercially available DD, DCIP (dichlordiinpropyl ether), and the like.

実施例 １ １．５，５．５−テトラクロルペンテン−２５０部にケ
ロシン５０部を均一に混合して油剤とする。Example 1 50 parts of kerosene is uniformly mixed with 250 parts of 1.5,5.5-tetrachloropentene to prepare an oil agent.

施用に当っては、土壌に一定間隔の穴を堀り所定量を注
入した後直ぐに土で穴を閉ぐ（注入処理）、土壌を薬剤
が良く浸透するように充分に耕やした後、その表面ζこ
ジョー口などで潅注する（表面潅注処理）、また必要に
応じてロータリーなどで１０〜２０ＣＩ′ｎの深さに混
和する（土壌混和処理）、或いは土壌に溝をつくり潅注
し必要に応じて覆土し、又は混和する（溝処理）等の方
法にて用いる。For application, holes are dug at regular intervals in the soil, a predetermined amount is injected, and then the holes are immediately closed with soil (injection treatment). Irrigation can be carried out using a surface jaw or the like (surface irrigation treatment), or if necessary, it can be mixed to a depth of 10 to 20 CI'n using a rotary (soil mixing treatment), or if necessary, it can be irrigated by making grooves in the soil. Depending on the situation, use methods such as covering with soil or mixing (groove treatment).

実施例 ２ １．５，５．５−テトラクロルペンテン−２８５部、白
灯油１０部、乳化剤５部を均一に混和して乳剤とする。Example 2 285 parts of 1.5,5.5-tetrachloropentene, 10 parts of white kerosene, and 5 parts of an emulsifier are uniformly mixed to form an emulsion.

施用に当っては所定量の水で希釈して実施例１と同様の
方法にて用いる。For application, it is diluted with a predetermined amount of water and used in the same manner as in Example 1.

実施例 ３ １．５，５．５−テトラクロルペンテン−２２０部、ケ
イソウ士及びカープレックス混合物７５部、アルキルベ
ンゼンスルホン酸ソーダ５部を混合粉砕して水利剤とす
る。Example 3 220 parts of 1.5,5.5-tetrachloropentene, 75 parts of diatomaceous and carplex mixture, and 5 parts of sodium alkylbenzenesulfonate were mixed and ground to obtain an irrigation agent.

施用に当っては所定量の水で希釈して実施例１と同様の
方法にて用いる。For application, it is diluted with a predetermined amount of water and used in the same manner as in Example 1.

実施例 ４ １．５，５．５−テトラクロルペンテン−２３０部をケ
イソウ土とベントナイトを４：１の割合で混合し、水で
練ってペレット化して乾燥して得た担体粒子に含浸させ
て粒剤とする。Example 4 230 parts of 1.5,5.5-tetrachloropentene was impregnated into carrier particles obtained by mixing diatomaceous earth and bentonite in a ratio of 4:1, kneading with water, pelletizing, and drying. Take the form of granules.

施用に当っては土壌表面に均一に散粒又はすじまきして
混和する或いは土壌に溝をつくり均一に散粒して直ちに
覆土する等の方法で用いる。When applying, use methods such as scattering or streaking the particles uniformly on the soil surface and mixing them in, or by making grooves in the soil, scattering the particles evenly, and immediately covering the soil.

実施例 ５ １．５，５．５−テトラクロルペンテン−２５部にクレ
ー及びカープレックスの混合物９５部を加え粉砕混合し
て粉剤とする。Example 5 95 parts of a mixture of clay and Carplex were added to 25 parts of 1.5,5.5-tetrachloropentene and ground and mixed to form a powder.

施用に尚っては散布機などで土壌表面に均一に散布して
混和する等の方法で用いる。When applying it, use a method such as spreading it evenly over the soil surface with a spreader and mixing it.

次に代表的な試験例を示して本発明化合物の殺線虫効果
について更に具体的に説明するが比較対象のため化学構
造上本発明化合物と近縁の塩素化炭化水素及び市販の殺
線虫剤の主なものについて試験をした結果も併せて示す
。Next, the nematicidal effect of the compounds of the present invention will be explained in more detail by showing representative test examples. The results of tests on the main agents are also shown.

試験例 １ 表面積約２００ｄ高さ１５ｃｍ、の素焼性ポットに根コ
ブ線虫が棲息する土壌を入れ、これに所定量の供試薬剤
を加えて充分に混和する。Test Example 1 A clay pot with a surface area of approximately 200 d and a height of 15 cm is filled with soil inhabited by root-knot nematodes, and a predetermined amount of the test chemical is added thereto and thoroughly mixed.

薬剤処理７日後にキュウリの稚苗をポット当り３本宛移
植し、１４日後にその根を取り出し調査した。Seven days after the chemical treatment, three young cucumber seedlings were transplanted per pot, and the roots were removed and examined after 14 days.

形成された根コブ数によって階級値を０〜４の５段階に
分は次式によって算出した根コブ指数をもって寄生度を
求めた。The degree of parasitism was determined using the root gall index calculated by the following formula, which was divided into five grades from 0 to 4 depending on the number of root galls formed.

Σ（階級値）×個体数 根コブ指数−Ｘ １００ 全調査個体数×４ 尚、残った各栽培土壌を良く撹拌した後５０，９宛採取
し、ベールマン漏斗法により線虫を分離し、分離液１ｒ
ｎｌ中の線虫の数を計数してネコブセンチュウの殺線虫
率を判定した。Σ (class value) x number of individuals Root Cobb index - liquid 1r
The number of nematodes in nl was counted to determine the nematicidal rate of Nematode nematode.

但し、無処理の場合にはネコブセンチュウ数は６０匹、
その他のセンチュウ数は８０匹であった。However, in the case of no treatment, the number of cat nematodes is 60,
The number of other nematodes was 80.

試験例 ２ 試験例１の方法に於いて試験用ポットに所定量の薬剤を
潅注した後２〜３ｃＴＬの覆土をした他は全て試験例１
と同様にネコブセンチュウの寄生度、殺線虫率を求めた
。Test Example 2 The method of Test Example 1 was followed except that the test pot was irrigated with a predetermined amount of chemical and then covered with 2 to 3 cTL of soil.
In the same manner as above, the degree of parasitism and nematocidal rate of Nematode nematode were determined.

Claims (1)

【特許請求の範囲】[Claims] ｉ １，５，５．５−テトラクロルペンテン−２を有
効成分とする殺線虫剤。i A nematicide containing 1,5,5.5-tetrachloropentene-2 as an active ingredient.